Potassium Hydroxide → 2-(2,4-dichlorophenoxy)-2-methylpropanoic acid

HRID 1400241Notes

Reaction equation

HRID 1400241 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:5]=1[O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10]CC)=[O:9]>O.CCO>[Cl:3][C:4]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:5]=1[O:6][C:7]([CH3:14])([CH3:13])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 682839HCID 682839, compound2×

Product 1

HCID 2514232-(2,4-dichlorophenoxy)-2-methylpropanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of KOH (2.48 g, 44.2 mmol, 15 eq) in H2O (12 mL) was added a solution of ethyl 2-(2,4-dichlorophenoxy)-2-methylpropionate (compound 5; 0.80 g, 2.89 mmol) in EtOH (12 mL). The solution was stirred at room temperature for 4 hours, then excess EtOH was removed under vacuum. The remaining aqueous solution was washed with EtOAc (10 mL), then acidified with concentrated aqueous HCl. The aqueous mixture was then extracted with EtOAc (10 mL), and the organic extract dried over Na2SO4, filtered, and evaporated to yield a thick, colorless oil which was used without further purification: 1H NMR (CDCl3) δ 7.42-7.41 (d, 1H), 7.19-7.15 (dd, 1H), 7.04-7.01 (d, 1H), 1.64 (s, 6H).

Workup

  1. customexcess EtOH was removed under vacuum
  2. washThe remaining aqueous solution was washed with EtOAc (10 mL)
  3. extractionThe aqueous mixture was then extracted with EtOAc (10 mL)
  4. extractionthe organic extract
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a thick, colorless oil which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-b275cd786f6e4ed3b9c392a411fcac84
Source dataset
uspto-grants-2014_12
Patent number
US08906945B2

Reaction notes

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